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Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one
The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent m...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690470/ https://www.ncbi.nlm.nih.gov/pubmed/31417776 http://dx.doi.org/10.1107/S2056989019009435 |
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author | Syed Abuthahir, S. NizamMohideen, M. Mayakrishnan, S. Uma Maheswari, N. Viswanathan, V. |
author_facet | Syed Abuthahir, S. NizamMohideen, M. Mayakrishnan, S. Uma Maheswari, N. Viswanathan, V. |
author_sort | Syed Abuthahir, S. |
collection | PubMed |
description | The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent molecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intramolecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal of I, molecules are linked by N—H⋯π interactions, forming chains along the b-axis direction. A C—H⋯π interaction links the chains to form layers parallel to (100). The layers are then linked by a second C—H⋯π interaction, forming a three-dimensional structure. In the crystal of II, the two independent molecules (A and B) are linked by N—H⋯O hydrogen bonds, forming –A–B–A–B– chains along the [101] direction. The chains are linked into ribbons by C—H⋯π interactions involving inversion-related A molecules. The latter are linked by offset π–π interactions [intercentroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure. |
format | Online Article Text |
id | pubmed-6690470 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-66904702019-08-15 Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one Syed Abuthahir, S. NizamMohideen, M. Mayakrishnan, S. Uma Maheswari, N. Viswanathan, V. Acta Crystallogr E Crystallogr Commun Research Communications The title compounds, 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one, C(22)H(17)NO(2), (I), and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one, C(14)H(17)NO(2), (II), are new isocoumarin derivatives in which the isochromene ring systems are planar. Compound II crystallizes with two independent molecules (A and B) in the asymmetric unit. In I, the two phenyl rings are inclined to each other by 56.41 (7)° and to the mean plane of the 1H-isochromene ring system by 67.64 (6) and 44.92 (6)°. In both compounds, there is an intramolecular N—H⋯O hydrogen bond present forming an S(6) ring motif. In the crystal of I, molecules are linked by N—H⋯π interactions, forming chains along the b-axis direction. A C—H⋯π interaction links the chains to form layers parallel to (100). The layers are then linked by a second C—H⋯π interaction, forming a three-dimensional structure. In the crystal of II, the two independent molecules (A and B) are linked by N—H⋯O hydrogen bonds, forming –A–B–A–B– chains along the [101] direction. The chains are linked into ribbons by C—H⋯π interactions involving inversion-related A molecules. The latter are linked by offset π–π interactions [intercentroid distances vary from 3.506 (1) to 3.870 (2) Å], forming a three-dimensional structure. International Union of Crystallography 2019-07-09 /pmc/articles/PMC6690470/ /pubmed/31417776 http://dx.doi.org/10.1107/S2056989019009435 Text en © Syed Abuthahir et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/ |
spellingShingle | Research Communications Syed Abuthahir, S. NizamMohideen, M. Mayakrishnan, S. Uma Maheswari, N. Viswanathan, V. Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one |
title | Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one |
title_full | Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one |
title_fullStr | Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one |
title_full_unstemmed | Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one |
title_short | Crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1H-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1H-isochromen-1-one |
title_sort | crystal structures of two new isocoumarin derivatives: 8-amino-6-methyl-3,4-diphenyl-1h-isochromen-1-one and 8-amino-3,4-diethyl-6-methyl-1h-isochromen-1-one |
topic | Research Communications |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6690470/ https://www.ncbi.nlm.nih.gov/pubmed/31417776 http://dx.doi.org/10.1107/S2056989019009435 |
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